Process of making borneol.



' ALBERT HESSE, or BERLIN,'GERMANY, ASSIGNOR 'ro CHEM ISCHE FAB- RIKAUF ACTIEN, (VORM.

E. SCHERING) OF BERLIN, GERMANY PROCESS OF MAKING BORNEOL.

Specification of Letters Patent;

Patented July 17,1906.

Application filed November 4, 1905. Serial No, 285,870.

To all whom it may concern.-

- Be it known that I, ALBERT Hnssn, doctor of philosophy, chemist, a subject of the German Emperor, residing at Berlin, Kingdom of Prussia, German Empire, have invented a new and useful Improvement in the Manufacture of Borneol, of which the following is a i specification.

I have "found that the magnesium coinpounds of the hydrohaloids of pinene (pinene hydrochlorid, pinene hydrobromi d,. i-inene hydroiodid) absorb oxygen very readily and are then transformed into complex magnesium compounds, which when decomposed by dilute acids form borneol. '5

The magnesium compounds of thehydrohaloids of pinene are'best produced in the manner described in my applicatio'n-for Improvements in the manufacture of organic ma esium compounds. According to thls app ication a'solution of the pinene hydrohaloid is caused'to react upon magnesium in the presence of a catalytic reagent-for exam ple, a suitable organic halogen compound, such as methyliodid, ethyliodid, ethylbromid benzene bromid; benzene iodid, benzylchorid, bornyliodid, and-the like. Preferably an etherealfsplution'ofthc said alliyl or aryl halogen compounds is first alloive to react upfdn' magnesium and then a-solution of the pinene hydrohaloid' isadded to the mixture; To manufacture borneol, for instance,

' from pinene hydrochlorid,which is the cheap est starting material, I proceed as' follows: 0.2 kilogram of ethylbromid dissolved in 0.8

. kilogram of dry other is poured over 1.4 kilograms of magnesium. After stirring for a short time an energetic reaction takes place.-

Before the reaction is complete a solution of ten kilogramsof pinene hydrochlorid in siX' kilogramsof dry etlier is rad-ually allowed to flow into the mixture,"w ch is ,kept in con-- tinuous movement. The addition of' the until oxygen is no longer absorbed, the vessel with Water.

in which the reaction takes place beingcooled Ur on the addition of ice and dilute acids until a slightly-acid reaction is given the product of the reaction separates 1 into tfivo layers. The lower aqueous layer i's 5 5 drained off. The ethereal layer, which. is; neutralized if it has an acid reaction, is then) dried and freed from other by distillation:'-; The product thus obtained, which is' cru deji borneol, is purified by recrystallization from a suitable solventsuch as petroleum-ether, I alcohol, benzeneor separated from theini. purities by transformation intoits p'hthali acid ester. In this Way the magnesium com pounds. of the. hydrohaloids of "pinene are nearly quantitatively transformed into bOI'f' neol.

In referring in the claims to oxygen I desire to embrace not only substantially pure oxygen'for instance, air.

I claim as myinventron- 3 .1. The process of manufacturing borneol,

oxygen, but also suitable gases which contain -vvhich .consists in causing oxygen to react u "on. the magnesium compounds of pinene h'ydrohaloids, decomposing the resulting complex ma nesium compounds by dilute acids, and iso ating the formed borneol, substantially as set forth l 2. The process of manufacturing bornol, which consists in causing oxygento react uponthe magnesium compound of pinene hydrochlorid, decomposing the resulting com plex magnesium compoundfby dilute acids, and isolating the formed borneol, substan tially as set-forth. o 3. The process of manufacturing borneol, Which consists in causing a solution of a pinene hydrohaloid to react upon magnesium in' the presenceof a catalytic reagent, passing oxygen throu h the magnesium compoun thus produce decomposing the oxidized magnesium compound by diluteaoids, and isolating the formed borneol, substantially as set forth. r 9 5 .r 4. The process of manufacturing borneol, which consists in causing an ethereal solution of a suitable organic halogen compound to react upon ma nesium, then adding a solution In t4 stimony whereof I hate signed my of pinene hy rochlorid to the mixture, passname o this specifioation in the presence of decomposing the oxidized magnesium coln- Witnessesi ing oXy on through the magnesium comtwo subsoribing Witnesses, pound o pinene hydrochlorid thus produced, ALBERT HESSE.

pound by dilute acids, and isolating the. HENRY HASPER, formed borneol, substantially gs set forth. 'WOLD MAR HAUrT." 

